


Will Halstead Imagines

by sweetblink



Series: Chicago Med Imagines [1]
Category: Chicago Med
Genre: Gen, Imagines from Tumblr, Loving Will Halstead, Protective Will Halstead, Soft Will Halstead, Will Halstead Imagine, Will Halstead imagines, is that even a tag, my tumblr to be exact, oh well I just made it, posts from tumblr, sometimes it will be sister!reader & Will Halstead, sometimes stupid Will Halstead lol, what more can be added for Will Halstead
Language: English
Status: In-Progress
Published: 2019-09-26
Updated: 2019-09-25
Packaged: 2020-10-28 12:20:25
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 3
Words: 3,641
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20778464
Author URL: https://archiveofourown.org/users/sweetblink/pseuds/sweetblink
Summary: Collection of Will Halstead imagines from my tumblr





	1. Halstead Night Out

**Summary for the Chapter:**

> _Requested by: yes_
> 
> _Chicago PD/Med request of the Halstead brothers having a sister and it’s basically be some good ole fashion sibling bonding? Whether it be some friendly sibling competition or embarrassing each other?_
> 
> _Warning: none really, just brotherly love._

“Alright, I know what will make everything less boring.” Jay said, walking in living room, as he entered the apartment.

You and your brother, Will, looked up at Jay in confusion. “Yeah, and what exactly is that?” you asked, looking back at the TV, that for some miracle, was playing a rerun episode of one of your favorite show, Glee.

“Let’s go out and have some fun.” Jay said. Will just rolled his eyes and threw some popcorn at his face, Jay was about to do the same thing back, when you gasped loudly making him stop, and looked towards you.

“Let’s go rollerskating!” You squealed, jumping up from the couch. Will groaned and pouted.

“Why do you get to choose?” Will whined.

“Stop whining, you’re an adult not a kid, and because I’m the baby of the family, and you guys love me.” You playfully replied. Jay and Will just shared a look.

Will shook his head, and turned to Jay. “This is our faults, we spoiled the hell out of Y/N.” he told him, Jay just shrugged, and nodded.

You let out a squeal. “I’m go get ready.”

Jay just chuckled and sat besides his brother. “For the record, you’re the one that spoiled Y/N the most. This is mostly your fault.”

“Have you tried saying no to her?” Will asked. Jay sat there silently and Will laughed. “Exactly.”

They sat back down, watching the show waiting for the youngest to come out dressed. After a few minutes, Y/N walked back into the living room with her backpack purse and grabbed the her shoes by the door, Jay looked up and he frowned. “Hey, what are you wearing young lady.”

Will looked up and frowned. “No, go change that shirt.”

You looked down at your shirt, and it was a choker, chest open type blouse. “But guys.” you pouted, you gave them your iconic puppy face, and you can see your brothers starting to cave in.

“It’s either you change or shirt, or I’m bringing all your embarrassing photos.” Jay threaten, you turned to Will and gave him the puppy eyes, he looked like he wanted to say no, but then he just let out a deep sigh.

“Alright fine, but if a guy looks at you the wrong way, he will be sorry.” Will said defensively. You looked over to Jay.

“Fine, but we’re not responsible to what happens to the guys who stare at you the wrong way.” Jay said as well. You just let out a squeal, and rushed over to them, and wrapped your arms around them both. 

“You guys are the best brothers ever.” You told them seriously. Will and Jay just hugged you back and kissed each side of your hair.

“Alright, let’s get the Halstead night out, on the go.” Jay said, grabbing the keys.

Y/N, Will, and Jay all made their way out to the car, Jay driving, Will in the passenger seat, while you sat in the back. The ride to the rink, you either spent it singing loudly with Will occasionally joining or arguing with Jay about his bad taste in music.

“So, who’s paying for the entrance?” You asked them, smirking a bit.

Jay turned to Will, and back on the road, while Will just looked back at you. “Why are you smirking?” he asked.

“Oh, I don’t know, maybe it has to do with one of you paying.” you replied.

“Why us, and not you?” Jay asked.

“Because, if you guys remember, the last time we went out, was when we went to the movies to see that horror movie, and I paid for all three of our tickets, it’s either one of yours turn.”

Jay had stopped at the red light, and turned to Will. “Rock, paper, scissors, loser pays.” he said. Will nodded, and they quickly played, only for Will to lose, you let out a small giggle and patted his shoulder. 

Finally, they all arrived at the skating rink, with Will grumbling about paying, while you just rushed up to the skate rentals. Jay and Will left to get their drinks, and both went to go find a table, watching you act like a small child. You rushed over to Will and tackled him into a hug.

“Are you guys gonna get your skates?” You asked. Jay looked over at you, and smiled.

“Only if you agree to race me.” Jay challenged.

“I’ll be out there waiting.” You replied, smirking at him, as you skated away.

“You do realize that you’re gonna lose right, Jay?” Will taunted him. Jay just scoffed.

“Watch me win this race.” Jay said, heading towards the rental, Will just let out a laugh.

“Your funeral, bro.” Will teased.

Jay waited for the dude to give him the skates, and he quickly put them on, while Will continued to tease him, by the time he was finished, you just skated past him in full speed, startling him. Will grabbed his phone out, ready to record you both.

“Ready Jay Jay?” You asked in a teasing voice. Jay rolled next to you, smirking.

“Are you ready?” he asked back. You just smiled and nodded, you both rolled to where Will was standing.

“Count us off, Willy Will.” You told him smirking, crouching a bit.

Will just laughed. “On your mark.” Jay started to crouch a bit as well. “Get Set.” Y/N start to giggle a bit. “Go!” Jay and Y/N both took of skating, Will just chuckled watching Jay pushing you lightly. Jay was taking the lead at first, almost taking the win, when all of the sudden you skated right past him, winning.

“And the winner is, Y/N Halstead!” Will yelled. Jay just stood there stunned, while you skated over to Will and you started to celebrate your win.

“But… but, I was winning, what the hell Y/N/N?” Jay asked, skating towards you both.

“Never underestimate the power of Baby Halstead.” You teased back.

Jay shook his head in disbelief, while you and Will just laughed at him.

“Next time, Y/N/N, I will beat you next time.” Jay said, smiling at you.

“Keep telling yourself that”

**Notes for the Chapter:**

> If you are interested, follow, and do all the fancy stuff people do on my Tumblr lol
> 
> [my tumblr](https://www.tumblr.com/blog/sweetblink)


	2. Surprise, Surprise

**Summary for the Chapter:**

> _Requested by: yes_
> 
> _And #4 with Will Halstead please?_
> 
> _#4. “We’re so gonna get caught, and I’m blame it on you.”… “Hey, you said you wanted to do this, therefore it’s not my fault.”_
> 
> _Warning: FLUFFFF, reader is Connor’s sister, and a detective._

“I’m warning you right now, if you hit me with that, you’ll cook dinner.” you warned.

Will Halstead froze, and dropped his Nerf gun, chuckling a bit. “Do you have eyes in the back of your head, babe?”

You chuckled as you turned the stove on low, and turned to him. “No, I just have spectacular hearing, also, I’m a detective, remember.”

Will laughed and walked over to you, and kissed your head. “I’m home.” he greeted.

“I can see that.” You laughed. “How was your shift?”

“Chaotic, but I saved my patient today.” he replied.

You gave him a soft smile and checked the food once more, and then turned the stove off, you pulled Will out of the kitchen and towards the room, in hopes of giving him a small massage. “So I was thinking.”

Finally entering the room, Will took off his scrub shirt, and his undershirt, and turned to you. “Uh oh, that’s a bad sign.” he teased.

You scoffed and pushed him on the bed, while he just laughed. “You’re so mean.” you whined.

Will just smiled and pulled you towards him, making you straddling his lap. “I’m kidding, so what were you thinking.”

“Connor’s birthday is coming up, and I wanna surprise him with a small birthday dinner, and leave him a big surprise gift.” You replied, massaging his shoulder. “Just wanna spoil him a little, I know things are all tensed with Dr. Bekker, so I want to cheer up my older brother.

"Are you sure?” Will asked. “I mean he’s been moody lately, and the tension between Bekker and him keeps getting worse.”

You sighed. “I don’t understand them, they like a love/hate thing going on. But anyways, are you in?”

Will just stared at you and nodded. “Fine, but only because I know you’d continuing badgering me if I said no.”

You smiled innocently and just giggled. “I would never.” 

Will just chuckled and started to kiss your neck, you let out small sigh, and exposed your neck a bit more. “We can eat dinner a bit late, right?” he asked.

***************************

“I’m literally questioning my sanity right about now.” Will whispered. You let out a low scoff, and elbowed him, he let out a small grunt.

“Shut up.” You whispered back.

_**“We’re so gonna get caught, and I’m blame it on you.”**_ Will groaned quietly.

_**“Hey, you said you wanted to do this, therefore it’s not my fault.”**_ You whispered back fiercely.

“It’s still gonna be your fault.” Will mumbled. You just rolled your eyes, and broke into your the apartment.

You and Will silently tip toed into your brother’s apartment, you were about to set his gift bag on the kitchen counter, when you both heard load moans, you froze and turned to stare at your boyfriend, with eyes wide.

“Oh god.” you moaned in agony. “Nope, we’re leaving.” You rushed out to the apartment when you bumped into a table, you let out a hiss of pain, and dropped a vase, you cursed, when you heard the room go silent. You quickly straighten out, turned the lights on, grabbed your keys, and held in your hands. “Quick, act natural.” you hissed at Will.

Will rushed to the door, and acted like he was just closing it, you were facing him, silently giggling.

“Y/N? Will?” you heard Connor.

You turned to your brother, and smiled widely. “Hi big bro, I knocked and you didn’t open so I assumed you were asleep, and decided to use my key to open it.”

Connor looked confused. “Y/N, it’s midnight, what are you doing here?”

You sighed. “My apartment building smelled horribly, so I complained to Will, he called the fire department to check it out, and decided to come over.” you somewhat lied easily.

“Connor, who’s at the doo-” A blonde girl appeared next to Connor, and you saw her tense up when she saw you. “Oh, and you are?”

“Y/N, Y/N Rhodes.” you replied evenly.

The blonde girl gave you a tight smile and you turned to your brother. “I know I came late, and uninvited, but we please stay the night? I’ll make your favorite birthday breakfast, in the morning.”

Connor facial’s changed into a more happy one, and smiled. “Of course you can stay baby girl.” You squealed and rushed to hug him.

“Oh, also, this is for you.” Handing him the gift bag. Connor smiled and accepted it. He reached in and grabbed it, you looked back at Will and smiled.

“Congratulations, Daddy?” Connor asked confused. You let out a small gasp. “Wait a minute.” Connor looked up at Will shocked, while he did the same thing, and then they turned to you.

“Babe. You got the wrong bag!” You squeaked in horror.

“You’re pregnant?!” they both yelled.

Your mouth dropped to form an O, and finally let out a small smile. “Surprise?” you said to Connor, and then turned to Will “Surprise.”

“I’m gonna be a dad.” Will breathed out. “Oh, I’m gonna be a dad?”

You looked at him and smiled. “Yes Will, you’re going to be a dad.” Will rushed over to you, and picked you up.

“Oh baby.” Will said, kissing you all over your face. “I gotta call Jay.” he said excitedly, rushing outside the apartment to call him. You turned back to your brother. and he walked over to you.

“So I’m guessing that wasn’t my actual present.” He teased. You giggled and shook your head no.

“That was supposed to be Will’s, your present is actually something different, I was going to surprise you with a onesie and a shirt that said #1 Uncle and #1 Nephew, after I revealed my pregnancy to Will.” you explained smiling. Connor just chuckled and hugged you tightly.

“You’re growing up way to fast, what happened to no boyfriends till you were 50.” Connor teased, getting a bit emotional, you just sniffed and giggled.

“That went out the window, when I fell in love with Will.” You said, giving the blonde girl a watery smile, Bekker, smiled you both and left to the kitchen.

Will finally came back in, smiling very wide, and plucked you away from your brother, Connor laughed, and left to join his, whatever it was to him, in the kitchen. “Jay sounded happy after I broke the news to him.” He told you.

“Is that right?” you teased. 

Will smiled and nodded, he placed a hand over your stomach and rubbed small soft circles. “You just made me the happiest man alive.” he told you, kissing the side of your hair. You smiled and relaxed into his side.

“I love you.” You breathed out.

“I love you too, baby.” Will replied, peppering you with soft kisses.

**Notes for the Chapter:**

> If you are interested, follow, and do all the fancy stuff people do on my Tumblr lol
> 
> [my tumblr](https://www.tumblr.com/blog/sweetblink)


	3. To Let Go

**Summary for the Chapter:**

> _Requested by: yes_
> 
> _Okay i know your requests are closed right now, but i just finished rewatching the one chicago crossover and i really really need one where reader is a female firefighter and shes Halsteads youngest sister and she scolds them for fighting at med, CAN YOU PLEASE WRITE AN IMAGINE FOR THAT?!?_
> 
> _Warning: all the emotional trauma it left me and i’m pretty sure everyone else. Also reader is dating Otis._

Y/N Halstead forced herself to remain calm, she was constantly shifting on her spot and pacing, to keep herself from running towards the stairs to go find her father. Chief Boden noticed and wrapped his arm around her.

“Hey, your old man is gonna be fine.” Boden muttered.

Y/N snorted. “Chief, you know better to sugarcoat things.” you replied back. Boden just let out a small chuckle and focused back on what was going on, finally Jay walked back inside and stood next to you. “Anything on dad?” he asked.

You shook your head. “No, you said that dad was supposed to be home.”

“He was.” Jay let out a small snarl, he grabbed his phone and marched back up to the man, Y/N can hear how her older brother described their father, and she rolled her eyes, when she noticed that Otis finally made his way down, she rushed over to him, smiling

She slowed a bit when she noticed Otis freeze. “Otis, babe, what’s wrong?” you asked, walking towards him where the elevator had opened. He said nothing, but you turned to the elevator and saw the smoke started to clear and that’s when you saw them.

A small cry left your lips and turned to Otis, who quickly pulled you to his chest. There in the elevator in the corner sat the dead burned mother and baby that Otis had been searching. Otis finally snapped out of it, and pulled you away from them.

“Hey, you’re going to be okay?” Otis asked you softly.

You looked at him in a pained expression. “They didn’t deserve to go out like that.” you whispered. Otis just gave you a small pained expression.

“I’ll go tell Chief Boden.” Otis said, he just pressed a kiss to your hair, and walked away, you just watched him walk off and turned back to the bodies, you spent about a minute starting at them, when you heard Casey.

“Chief, I got two victims on 25, Jay’s and Y/N’s father, and his friend.”

At Casey’s words, you knees buckled, and you fell to the ground, letting out a huge breath of relief that you were didn’t know you held, and began to sob. Jay rushed over to you, and helped you back up, pulling you into his arms, rubbing your back.

“He’s okay, he’s gonna be okay.” Jay muttered, you just hugged your older brother back tighter and nodded, you decided to hide your face to his chest, not wanting the others to see you in a weak state.

Things to got a bit worse when you heard that Stella inhaled so much smoke, it was critical.

*******************

Hours had gone by and you were in between watching over your dad, and looking over at Stella. You were walking back when you saw nurses rushing towards your father’s room, you picked up your pace and watched as they tried to revive your dad.

You tried to say something, but the words caught in your throat, making it impossible for you to even speak, Jay was by your side, speaking to you, but you couldn’t. After a few minutes they had managed to control your dad, Will stood and watched as Dr. Lanik checked your father over.

You just stared at your dad, and ignored the men all around, it wasn’t until you heard brain dead when you snapped back to reality. “I’m sorry, what?” you asked.

All three turned to you, and tears began to form around your eyes. Will moved to your side. "I’m sorry, I will give you three to process things.“ Dr. Lanik said, as he excused himself out. You just turned to Will.

"He’s brain dead, Y/N. I’m afraid we can’t do much about this situation.” Will whispered to you. You stared at him for a minutes and then glanced back at dad who laid there, still, looking back at Will you nodded and moved to sit next your dad, while your two older brothers left the room. Both looking ready to argue and fight about what’s gonna happen next.

You sat on the chair for a while, and just stared at your dad, holding his hand. You stayed that way about thirty minutes talking to him. “Daddy, I don’t think I know how to let go.” You whispered. 

Silence engulfed the room, when you heard a commotion going outside, you were about to ignore it, when you heard Maggie calling for Otis’ name, panicking about the worst, you scrambled off the chair, and tripped your way out your dad’s room.

“Otis.” You gasped when you saw Otis on the floor, gasping for air. Rushing over to Maggie “Maggie, what happened?” you asked.

Maggie looked up at you, and shrugged. “I don’t know, one second I was asking if he was alright, and then he collapsed, I don’t know if its his gunshot, or something else.”

You nodded and helped the others place Otis on the gourney, the nurses were quick to hook him up and you stood by the door, watching them work. “Mags, you think you can check up my dad for me?” you asked, still staring at Otis.

Maggie looked up at you and her face fell a little. “Yeah, I would.” Turning back to her, you gave her a small smile and nodded at her and entered Otis’ room now that he was settled in his bed, listening to what the doctor was telling you.

Moments later, Dr. Charles entered, talking to you, waiting for Otis to wake up, when the both of you heard yells outside. “What the hell.” you muttered, standing up and looking out the room when you noticed that it was your brothers, fighting. “You help him Dr. Charles, I’ll take care of this.” you muttered, leaving. 

Angrily, you stromed up to them. “ENOUGH!” You yelled, pushing your older brothers away. “Jesus christ we’re in the hospital for God’s sakes, both of you get your head out of asses, you’re not the only two losing someone.”

Jay and Will both turned to you, both of them softening up when they saw you crying. “Y/N, we di-.”

“Leave.” You sneered. They both paused when you said that.

“Y/N, I have to be here.” Jay said.

“And I want you to leave, I want you guys to leave, take a walk, I don’t know, do something to clear your heads, but right now I want you both to leave me and dad alone.” You said, turning back to your dad, ready to go back into his room.

“Y/N, you’re being selfish, I need to be here.” Jay snarled, grabbing your arm. You let out a cry of pain, turning around you pushed him away, making him fall the ground. Your eyes widen at him, as Jay looked at you, distraught, while Will was ready to step in.

“I want you to leave, the both of you.” You whispered, clutching you arm. “I don’t want to see neither of you here for the next hour or so.” you said, walking back into the hospital room where your dad laid.

Will and Jay both stood there, watching, as you sat on the chair where Jay sat, and grabbed Dad’s hand. Not wanting to leave you, they watched as you began to let out a loud sob and abandoned the chair as you climbed onto the bed and laid next to him.

“We should’ve been strong for her.” Will muttered, Jay turned to him. “She’s the only that was much closer than dad than we were, and clearly everything is affecting her.”

Jay looked back at you, and let out a small sigh and stormed away, grabbing his phone out, talking to his team now. Will just stared down to the floor, and let out a small sigh and decided to back to work.

Hours later, after everyone was calm, and Will and Jay finally talked things out perfectly with no argument, they decided that it was finally time to pull the plug.

“I’m sorry Y/N, but we need to let go.” Jay told you softly, comprehending, you nodded and watched as Will called for the others.

The three siblings sat around the bed, as the three of you all watched Dad get taken off life support. You just sat there, watching as dad’s heartbeat started to slowing go towards 0, until all you heard was the flatline sound. 

Lips wobbling, you turned to your brothers with a lost look and tried to say something, but all the escaped your mouth was a pained cry, quickly Jay pulled you into his arms, Will came in and both of them squished you in a hug, that was the way the three of you stayed until it was time for everyone to return to work.

**Notes for the Chapter:**

> If you are interested, follow, and do all the fancy stuff people do on my Tumblr lol 
> 
> [my tumblr](https://www.tumblr.com/blog/sweetblink)


End file.
